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1st time, I was the first employee of a company that grew to over 150 people. It went bust in the first dot-com bubble bursting and I got nothing for my sizable number of options, except for a lesson in how easily CEOs can break promises regarding money held in escrow.

2nd time, I was the first employee of a company that never got bigger than 15 people. I had 2%, with a quarter of that vested (0.5%) The company was acquired and I got nothing except one week's notice that I might need a new job and a lesson in liquidation preferences.

This time around I'm getting 25 basis points, and I'm employee number 50 or so. We'll see if the third time is the charm, but to be honest, I truly don't care. Equity is nice to have but it's worthless until it's not.



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